Martha's Vineyard Rental Homes For Large Groups

Find a wonderful variety of Martha’s Vineyard vacation rentals for large groups and families. Find homes for large groups in Chilmark, Oak Bluffs, Edgartown, and other popular communities on Martha’s Vineyard. Whether you are looking for waterfront views, walking distance to the beach or close to downtown, find your perfect Martha’s Vineyard vacation home here!

Scroll to view Martha's Vineyard vacation rentals below. Contact us today if you would like to learn more about a specific property. Register with the site to save all of your favorite properties and receive email alerts when new listings come onto the market. If you already have an account, feel free to sign in.

 

Rental Price$4,000 to $12,000

Rental ID 134575

  • RTR Vacation Rental
  • Lease $4,000 to $12,000
  • Village Chilmark
  • Bedrooms 5
  • Bathrooms 3

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach! The house lies between West Tisbury (Alley’s General Store, 7A Foods, Farmer’s Market, Artisan’s Market, galleries, etc.) and Chilmark (Chilmark Store, Chilmark Tavern, Chilmark Community Center, etc.). It is also a short ride to Menemsha Village (fishing, fish markets, galleries, restaurants, and sunsets on the beach). This 1713 Mayhew farmhouse underwent a complete gut-renovation in 2017 and was reborn to honor its past while embracing today’s contemporary lifestyle. The house is fully air- conditioned and has Wi-Fi, high speed Internet and cable TV. A beautiful three-season porch was added to the back of the house. It is a relaxing place to sit, read, play a game, watch TV, or simply observe what is going on outside. The porch leads to a bluestone patio with a teak dining table with seating for 8 under a market umbrella along with a number of chairs to relax in and a gas grill. Adjacent to the patio is a large private outdoor shower. The house is surrounded by an expansive lawn bordered by stonewalls. The house is remarkably open on the first floor. The porch leads into a fully equipped cook’s kitchen with high-end appliances, quartz countertops and an island with seating. The dining room has a farmer’s table that seats up to 10 along with an additional sitting area by the fireplace. The library/media room is a cozy place to sit and talk, read by the fireplace, or binge watch that show you just never got to last year on a large flat screen TV. The final room downstairs is the first, of two, en suite master bedrooms (queen bed). It has a fireplace, flat screen TV, and a marble and tile bathroom. A French door leads from this bedroom to the bluestone patio. The central hallway contains a half bath and two stairways that lead to the second floor where you will find four additional bedrooms, (two queens, one twin and an en suite king), a full laundry and a large bathroom with an oversized tub/shower. The 2nd floor master bedroom (king bed) has a flat screen TV, an attached walk-in closet and en suite marble and tile bath. High quality linens and towels are provided throughout the house. The real bonus of this house is its key to Hancock Beach—located approximately 1.5 miles from the house down a private road. Hancock Beach is a premier private South Shore ocean beach adjacent to Chilmark Pond so that both can be enjoyed. Tenants can bring kayaks to the pond to explore this beautiful, unspoiled environment. Tenants also have access to Chilmark town beaches—Lucy Vincent and Squibnocket. Beach chairs, towels, umbrellas and coolers are all provided.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$2,990 to $6,990

Rental ID 134518

  • RTR Vacation Rental
  • Lease $2,990 to $6,990
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 4

With sweeping views of Vineyard Haven Harbor, this recently built, in-town luxury home, combines commanding water views with four levels of sophisticated and stylish living space, including two roof top decks, Home Theater, tournament Pool Room, Penthouse Lounge, and more. The main floor of Captain Spring House features an open Great Room designed for entertaining, with Living and Dining Ares, plus a large Gourmet Kitchen. The fully-equipped Chef s Kitchen features marble countertops, grand prep island/breakfast bar with seating for eight, Wolf and Sub Zero stainless appliance, two farmer sinks, double dishwashers, and wine refrigerator. There are hardwood floors and high ceilings throughout the home. All four bedrooms feature full marble baths with tub and shower, and flat screen TVs. The second floor Master Suite also has a glass walk-in shower and whirlpool with harbor views. The third floor Penthouse Lounge features phenomenal views, sectional seating, wet bar, and refrigerators. Best of all, walk out onto two large mahogany sun decks that face the harbor. One has outdoor shower. The lower level features both a Home Theater and a Pool Room Lounge. There is a tournament pool table and a fully-equipped wet bar. Captain Spring House sits quietly on a side street, just steps from downtown Vineyard Haven with its charming Main Street, restaurants, shops, beach, and ferry which is only 2 blocks away.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$25,000 to $30,000

Rental ID 132316

  • RTR Vacation Rental
  • Lease $25,000 to $30,000
  • Village Aquinnah
  • Bedrooms 4
  • Bathrooms 3

This Martha’s Vineyard property is a great vacation home to experience the beautiful island setting in the town of Aquinnah. This new 4 bedroom 3.5 bath home overlooks the Vineyard Sound with breathtaking panoramic views out to the Elizabeth Islands. With state of the art decor and interior furnishings, guests will enjoy environmentally sensitive, energy-efficient, and sustainable design. Just a short path to the private sandy beach, a great fishing spot and perfect for families with younger children. An outdoor shower, jacuzzi and sauna complete this spectacular, modern home.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$5,000 to $26,000

Rental ID 116944

  • RTR Vacation Rental
  • Lease $5,000 to $26,000
  • Village Edgartown
  • Bedrooms 11
  • Bathrooms 7

The Captain Morse House, at the corner of Morse and North Water streets, is one of Edgartown s finest homes. This newly renovated and exquisitely detailed home is perfect for your dream vineyard vacation. Includes eleven bedrooms and seven full baths on three floors, a formal living room and dining room, a family room, a game room, and two new gourmet kitchens all tastefully decorated with period furnishings and artwork. Current accommodations are for 23 people in 20 beds. On the North Water side facing the water are two spacious porches with partial water views of Edgartown Harbor and the Chappy Ferry. The harbor is just down the street and you have access to the town owned dock. The backyard features a spacious bricked patio with seating for ten where you can enjoy barbecue, croquet and other lawn games. There is off street parking for three cars (one large and 2-3 small). This is one of Edgartown s largest backyards.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $3,800

Rental ID 116638

  • RTR Vacation Rental
  • Lease $3,000 to $3,800
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 3

This lovely home is a modern farmhouse, built in 1998 with a very well-equipped kitchen, wooden floors and a fireplace. This home sits on 3 1/4 wooded acres and has all the sense of up-island privacy with only a short drive in to town, ferry, and shops. The downstairs den can be used as a 5th bedroom. With only 500 feet to Vineyard Sound and a short walk to the private association North shore beach this is a perfect summer rental.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,000 to $5,000

Rental ID 116330

  • RTR Vacation Rental
  • Lease $3,000 to $5,000
  • Village Chilmark
  • Bedrooms 4
  • Bathrooms 4

Sunrise from the ocean, sunset over Stonewall Pond and view towards Squibnocket Beach. Old Vineyard look and feel, an elegant and comfortable beach house with landscaped gardens. Recently built 500 sq ft addition includes ground floor MBR suite offering full amenities. On-site recreation includes kayaks, canoe, sail boat, clam rakes and buckets, as well as mountain bikes, road bikes, walking sticks and walking guides. For a more detailed list of services provided or arranged please contact your rental agent.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$4,000 to $7,500

Rental ID 138644

  • RTR Vacation Rental
  • Lease $4,000 to $7,500
  • Village Vineyard Haven
  • Bedrooms 4
  • Bathrooms 4

Brand new construction 2018, modern 4 bedroom home located on a quiet street though steps from downtown Vineyard Haven. First floor features open plan - sophisticated living and dining area with chef kitchen plus a master bedroom. You will find another master bedroom on the second floor and 2 more beautifully decorated bedrooms that share a bathroom.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$6,000 to $9,000

Rental ID 137764

  • RTR Vacation Rental
  • Lease $6,000 to $9,000
  • Village Oak Bluffs
  • Bedrooms 4
  • Bathrooms 4

Enjoy the perfect vacation in this updated gingerbread house, that offers gorgeous view from every angle. The home offers 4 en-suite bedrooms and plenty space for entrainment.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$3,300 to $5,500

Rental ID 135243

  • RTR Vacation Rental
  • Lease $3,300 to $5,500
  • Village Oak Bluffs
  • Bedrooms 5
  • Bathrooms 5

Bright, open totally redesigned, restored and expanded summer cottage on a quiet street in an historic and lovely neighborhood. Less than 1/2 mile from town. Open space plan for maximum interaction for everyday or special gatherings. Private nooks for book reading. Numerous large windows throughout home for a light, airy feeling. Beautiful hardwood floors and ceramic tiles throughout. Top of the line appliances and granite countertops in the kitchen. Many extras. First floor master suite and laundry. Ceiling fans in each bedroom as well as central a/c. A newly finished basement with large flat screen TV, ping pong table, and an extra 1/2 bath to spread out and relax. Rocking chairs on wrap around porch.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Rental Price$5,000 to $9,000

Rental ID 125617

  • RTR Vacation Rental
  • Lease $5,000 to $9,000
  • Village Edgartown
  • Bedrooms 4
  • Bathrooms 3

This well appointed four bedroom 3 bath home offers an open floor plan for relaxing. In the Great Room you have a 65 inch flat screen TV with surround sound, cable, HD, and Blue Ray DVD player,and a stereo system. With 2 acres of manicured lawns looking over the Katama Farm Institute, it is perfect for grilling and yard games. Just 1 mile to South Beach this is a prime time location!

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details